(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

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Chemical Name:(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan
CAS No.:862603-22-3
Molecular Formula:C₂₄H₂₉IO₄S
Molecular Weight:540.462
Hs Code.:

Synonyms:(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

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Chemical Property of (2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

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Technology Process of (2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

There total 14 articles about (2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 862603-74-5
Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester

: 862603-22-3
(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

Guidance literature:: With sodium iodide; In acetone; for 9h; Heating;
DOI:10.1021/ja0526867

Reference yield:

: (R)-4-Benzyloxymethyl-2-phenyl-[1,3]dioxane

: 862603-22-3
(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

Guidance literature:: Multi-step reaction with 13 steps

1.1: aq. AcOH

1.2: NaIO₄

2.1: Et₃N

3.1: N-methylmorpholine

4.1: NaI

5.1: 95 percent / N-Bu₃SnH; Et₃B

6.1: trifluoroacetic anhydride; pyridine

6.2: 84 percent / KOAc

7.1: 96 percent / MgBr₂*Et₂O

8.1: aq. OsO₄; 4-methylmorpholine N-oxide / acetone / 1.5 h / 20 °C

9.1: aq. NaIO₄ / ethanol / 1 h / 20 °C

10.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

11.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

12.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

13.1: 93 percent / NaI / acetone / 9 h / Heating

With 4-methyl-morpholine; pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethyl borane; tri-n-butyl-tin hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; In ethanol; dichloromethane; water; acetone; 6.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

: (S)-3-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propionaldehyde

: 862603-22-3
(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

Guidance literature:: Multi-step reaction with 4 steps

1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

2: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

3: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

4: 93 percent / NaI / acetone / 9 h / Heating

With 4-methyl-morpholine; sodium tetrahydroborate; triethylamine; sodium iodide; In ethanol; dichloromethane; water; acetone;
DOI:10.1021/ja0526867